Isoguanine: Difference between revisions

Isoguanine
Names
	IUPAC name 6-Amino-1,7-dihydropurin-2-one
	Other names 2-Hydroxyadenine
Identifiers
CAS Number	3373-53-3;
3D model (JSmol)	Interactive image;
ChemSpider	69351;
ECHA InfoCard	100.020.144
EC Number	222-157-6;
PubChem CID	76900;
CompTox Dashboard (EPA)	DTXSID00187406 ;
	InChI InChI=1/C5H5N5O/c6-3-2-4(8-1-7-2)10-5(11)9-3/h1H,(H4,6,7,8,9,10,11) Key: DRAVOWXCEBXPTN-UHFFFAOYAU;
	SMILES O=C1\N=C2\N=C/NC2=C(\N1)N;
Properties
Chemical formula	C5H5N5O
Molar mass	151.1261
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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Revision as of 10:46, 26 February 2019

Isoguanine or 2-hydroxyadenine is a purine base that is an isomer of guanine. It is a product of oxidative damage to DNA and has been shown to cause mutation.^[1] It is also used in combination with isocytosine in studies of unnatural nucleic acid analogues of the normal base pairs in DNA.^[2]^[3]

It is used as a nucleobase of hachimoji nucleic acids.^[4] In hachimoji DNA, it pairs with 1-methylcytosine, while in hachimoji RNA, it pairs with isocytosine.

References

^ Yang XL, Sugiyama H, Ikeda S, Saito I, Wang AH (1998). "Structural studies of a stable parallel-stranded DNA duplex incorporating isoguanine:cytosine and isocytosine:guanine basepairs by nuclear magnetic resonance spectroscopy". Biophys. J. 75 (3): 1163–1171. doi:10.1016/S0006-3495(98)74035-4. PMC 1299791. PMID 9726918.
^ Andrzej Jaworski, Józef S. Kwiatkowski, Bogdan Lesyng: „Why isoguanine and isocytosine are not the components of the genetic code", International Journal of Quantum Chemistry, Supplement: Proceedings of the International Symposium on Quantum Biology and Quantum Pharmacology, 1985, 28 (Supplement S12), pp. 209–216 (doi:10.1002/qua.560280720).
^ Christopher Roberts, Rajanikanth Bandaru, Christopher Switzer: „Theoretical and Experimental Study of Isoguanine and Isocytosine: Base Pairing in an Expanded Genetic System", J. Am. Chem. Soc., 1997, 119 (20), pp. 4640–4649 (doi:10.1021/ja970123s).
^ Hoshika, Shuichi; et al. (22 February 2019). "Hachimoji DNA and RNA: A genetic system with eight building blocks". Science. 363 (6429): 884–887. doi:10.1126/science.aat0971. {{cite journal}}: Unknown parameter |subscription= ignored (|url-access= suggested) (help)

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[1] Yang XL, Sugiyama H, Ikeda S, Saito I, Wang AH (1998). "Structural studies of a stable parallel-stranded DNA duplex incorporating isoguanine:cytosine and isocytosine:guanine basepairs by nuclear magnetic resonance spectroscopy". Biophys. J. 75 (3): 1163–1171. doi:10.1016/S0006-3495(98)74035-4. PMC 1299791. PMID 9726918.

[2] Andrzej Jaworski, Józef S. Kwiatkowski, Bogdan Lesyng: „Why isoguanine and isocytosine are not the components of the genetic code", International Journal of Quantum Chemistry, Supplement: Proceedings of the International Symposium on Quantum Biology and Quantum Pharmacology, 1985, 28 (Supplement S12), pp. 209–216 (doi:10.1002/qua.560280720).

[3] Christopher Roberts, Rajanikanth Bandaru, Christopher Switzer: „Theoretical and Experimental Study of Isoguanine and Isocytosine: Base Pairing in an Expanded Genetic System", J. Am. Chem. Soc., 1997, 119 (20), pp. 4640–4649 (doi:10.1021/ja970123s).

[SCI-20190222-4] Hoshika, Shuichi; et al. (22 February 2019). "Hachimoji DNA and RNA: A genetic system with eight building blocks". Science. 363 (6429): 884–887. doi:10.1126/science.aat0971. {{cite journal}}: Unknown parameter |subscription= ignored (|url-access= suggested) (help)

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 '''Isoguanine''' or '''2-hydroxyadenine''' is a [[purine]] base that is an [[isomer]] of [[guanine]].  It is a product of oxidative damage to DNA and has been shown to cause mutation.<ref>{{cite journal |vauthors=Yang XL, Sugiyama H, Ikeda S, Saito I, Wang AH |title=Structural studies of a stable parallel-stranded DNA duplex incorporating isoguanine:cytosine and isocytosine:guanine basepairs by nuclear magnetic resonance spectroscopy |journal=Biophys. J. |volume=75 |issue=3 |pages=1163–1171 |year=1998 |pmid=9726918 |doi=10.1016/S0006-3495(98)74035-4 |pmc=1299791}}</ref>  It is also used in combination with [[isocytosine]] in studies of unnatural [[nucleic acid analogues]] of the normal [[base pair]]s in DNA.<ref>Andrzej Jaworski, Józef S. Kwiatkowski, Bogdan Lesyng: „Why isoguanine and isocytosine are not the components of the genetic code", International Journal of Quantum Chemistry, Supplement: Proceedings of the International Symposium on Quantum Biology and Quantum Pharmacology, '''1985''', ''28''&nbsp;(Supplement S12), pp.&nbsp;209–216 ({{DOI|10.1002/qua.560280720}}).</ref><ref>Christopher Roberts, Rajanikanth Bandaru, Christopher Switzer: „Theoretical and Experimental Study of Isoguanine and Isocytosine:  Base Pairing in an Expanded Genetic System", ''[[J. Am. Chem. Soc.]]'', '''1997''', ''119''&nbsp;(20), pp.&nbsp;4640–4649 ({{DOI|10.1021/ja970123s}}).</ref>
+It is used as a [[nucleobase]] of [[hachimoji DNA|hachimoji nucleic acids]].<ref name="SCI-20190222">{{cite journal|last=Hoshika|first=Shuichi|display-authors=etal|date=22 February 2019|title=Hachimoji DNA and RNA: A genetic system with eight building blocks |journal=[[Science (journal)|Science]]|volume=363|issue=6429|pages=884-887|doi=10.1126/science.aat0971|subscription=yes}}</ref> In hachimoji DNA, it [[base pair|pairs with]] [[1-methylcytosine]], while in hachimoji RNA, it pairs with isocytosine.
 [[File:IG-iC DNA base pair.svg|thumb|none|upright=1.6|Isoguanine-Isocytosine-base-pair]]